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The 9th key habit of a rainmaker: Ask great questions

11 August 2016 - By Ben Paul

In my previous article in LawTalk 890, we looked at some of the key habits that the top rainmakers within legal firms demonstrate. The 9th habit being “ask really great open and engaging questions”.

Of course, the real skill isn’t just to ask these questions. You have to learn how to listen and respond to them.

The main trick that rainmakers manage to pull off with their questions is that they not only get to learn and understand more about the person, they actually start to develop and build trust.

Think about an occasion when you have first met someone and it’s gone really well, and you’ve genuinely wanted to see them again. The chances are they asked you questions which showed they were interested in you, your thoughts, and what you do. So are these people blessed with an intrinsic magic gift of great questioning skills? Maybe. More importantly, can these skills be learnt and developed by anyone? Absolutely.

Below I’ll look at some different types of questions and give some practical examples that you can hopefully use to start generating better conversations.

Start with some questions to understand who they are

It’s quite a good idea to ask simple opening questions like “How’s business?” or “How are things going?”

The response here can give you a quick insight into the other person’s behavioural preference. If they say something like “fantastic”, it is likely they live in a highly optimistic world and see opportunity, not risk, in things. What you might describe as a glass half-full person. If their response is more measured, then they are likely to be less so and perhaps a bit more focused on the now than the future. As with all questions, listening to and understanding the response is key.

Facts, facts, facts

For any of you who have read Hard Times by Charles Dickens, you’ll be able to appreciate that there is a lot more to understanding situations and people than you get from just cold hard facts.

If you ask “surface questions”, you will elicit facts. It is important to get some factual information, but too many surface questions can lead to a dull conversation that feels more like an interrogation. As an example, if someone says they had a great weekend with the family and you then ask them “How many kids do you have?” “What are their ages?” “What are their names?” “What school do they go to?” etc.

Too much hunting might hurt your prey

What we term as “hunt questions” are questions that look for issues or challenges that the other person may have.

Too many of these without exploring the issue further can make the other person feel like you are simply hunting for a problem which, big surprise, you have the perfect solution for.

There is also the classic question, meant well which is asked by many a legal professional: “What is your biggest challenge?” There is one major problem with asking a client or prospect about their challenges – and that is, that some of them won’t have any. So when you ask them about their challenges, you are actually giving them nightmares, and making them urgently want to leave the room.

Why not just ask them: “What are your three main priorities?”

Avoid one-way streets

The conversation is moving along but you’re stuck in one area. You might think that this is great as it’s in your area of expertise, but while it may be of interest to the other person are you certain it’s the most important thing to them right now? Take a pause and check in on your assumption.

At this stage, a great question to ask is: “Before we go any further, can I just check that this is the most important thing to you right now, because if it isn’t, what is?”

When offering this adjustment to the conversation, give the other person time to think and you may find that you learn something very different and genuinely interesting. We call this an “adjust question”.

Help them to paint a perfect picture

This is when you help the person you are talking to imagine or think about a positive future. We call these “paint questions”. They can have a dramatic effect on the conversation and really help unlock the other person’s thinking.

An example of this is: “In an ideal world, what would your business look like in three years?”

Firstly, this demonstrates that you care about the future of their business and want to understand more about it. Secondly, it helps them to think and reflect about the future, which is always valuable. Finally, through understanding this, you can continue the conversation to help your client to prioritise their strategies to achieve this.

Great chat, so what’s next?

A common thread I’ve found over years of coaching and advising people is that they feel they had a good meeting, but they have no idea what the next stage is, or how to follow up.

It can be as simple as they haven’t asked what the next steps are. We call these “engage questions” which help to uncover what the next steps are. To be clear, these aren’t hard sell sales questions such as: “Can I send you a proposal/credential statement?” That is a misguided question. This is because people are invariably polite and will say “yes”, and then never read the document you pour your heart into.

Rather ask them something simple like: “What do you see as the next steps?” Give them control and decide what the next stage in your relationship is.

You can develop the skills to SHAPE a successful conversation

So, in summary, great rainmakers ask great questions, and the good news is that this skill can be learnt and developed. It won’t come straight away but with continual practice it will undoubtedly improve.

These are some of the basics around what we call SHAPE Questions:

  • S is for Surface questions that illicit facts;
  • H is for Hunt questions that help you uncover challenges or issues;
  • A is for Adjust questions that seek clarification from the other person;
  • P is for Paint questions that help you understand the other person future aspirations; and
  • E for Engage questions, that help you understand what they see as the next steps.

As you start to understand these questions and use them, you’ll find the nature of your conversations change, for the better.

Ben Paul is Director New Zealand for The Business of Trust. Ben has over 17 years’ experience in both New Zealand and the UK in business development and as a coach/facilitator. He can be contacted at

Last updated on the 9th August 2016